Synthesis, crystal structure, DFT and biological activity of E-pyrene-1-carbaldehyde oxime and E-2-naphthaldehyde oxime
Year of publication
2020
Authors
Lasri, Jamal; Soliman, Saied M.; Elsilk, Sobhy E.; Haukka, Matti; El-Faham, Ayman
Abstract
The aldoximes E-pyrene-1-carbaldehyde oxime 1 and E-2-naphthaldehyde oxime 2 were synthesized, in ca. 90% yield, by treatment of pyrene-1-carbaldehyde or 2-naphthaldehyde, respectively, with hydroxylamine hydrochloride and sodium carbonate in MeOH. Compounds 1 and 2 were characterized by IR, 1H and 13C{1H} NMR spectroscopies, elemental analyses and single crystal X-ray diffraction (in the case of 1). The studied system (compound 1) showed significant amounts of H⋯H (44.4%), C⋯H (25.4%) and C⋯C (13.3%) intermolecular interactions in addition to the short N⋯H (5.9%) and O⋯H (6.2%) intermolecular interactions. These interactions affect the molecular packing of the studied system in the crystal. The structure of 1 was optimized using DFT calculations and the calculated structure was found to well agree with the reported X-ray structure. Moreover, compound 1 is polar with dipole moment of 0.764 Debye using B3LYP/6-311G(d,p) method. The antimicrobial activities of the newly synthetized oximes 1 and 2 and the previously reported E-1-naphthaldehyde oxime 3 and E-9-phenanthrenecarboxaldehyde oxime 4 were examined against various pathogenic microbes. The oximes 1 and 3 were recorded to be the most effective oximes as antimicrobial agents against the tested microorganisms. The increase of compound concentration lead to a higher antimicrobial activity and an increase of K+ flow from the microorganism.
Show moreOrganizations and authors
University of Jyväskylä
Haukka Matti
Publication type
Publication format
Article
Parent publication type
Journal
Article type
Original article
Audience
ScientificPeer-reviewed
Peer-ReviewedMINEDU's publication type classification code
A1 Journal article (refereed), original researchPublication channel information
Journal
Publisher
Volume
1207
Article number
127848
ISSN
Publication forum
Publication forum level
1
Open access
Open access in the publisher’s service
No
Self-archived
No
Other information
Fields of science
Chemical sciences
Keywords
[object Object],[object Object],[object Object],[object Object],[object Object]
Publication country
Netherlands
Internationality of the publisher
International
Language
English
International co-publication
Yes
Co-publication with a company
No
DOI
10.1016/j.molstruc.2020.127848
The publication is included in the Ministry of Education and Culture’s Publication data collection
Yes